Herbicidally active compositions

ABSTRACT

A quick acting liquid herbicidal composition comprises a major amount of a hydrocarbon oil and a 3,5,6-substituted uracil, the improvement comprising using as a co-solvent, a fatty acid having at least 12 carbon atoms in chain length.

United States Patent [191 Vartiak *Jan. 9, 1973 [54] HERBICIDALLY ACTIVECOMPOSITIONS [75] Inventor: Joseph F. Vartlak, Naperville, Ill.

[73] Assignee: Nalco Chemical Company, Chicago,

Ill.

[ Notice: The portion of the term of this patent subsequent to Dec. 21,1988, has been disclaimed.

[22] Filed: Feb. 8, 1971 [21] Appl. No.: 113,599

Related US. Application Data [63] Continuation-impart of Ser. No.418,343, Dec. 14,

1964, Pat. No. 3,628,942.

[52] US. Cl ..71/92, 71/79, 71/DIG. 1 [51] Int. Cl. ..A0ln 9/00 [58]Field of Search ..7l/92, DIG. l, 79, 93, 117

Primary Examiner-James 0. Thomas, Jr. Attorney-John G. Premo, Charles W.Connors and Edward A. Ptacek [5 7] ABSTRACT A quick acting liquidherbicidal composition comprises a major amount of a hydrocarbon oil anda 3,5,6-substituted uracil, the improvement comprising using as aco-solvcnt, a fatty acid having at least 12 carbon atoms in chainlength.

3 Claims, N0 Drawings HERBICIDALLY ACTIVE COMPOSITIONS This is acontinuation-in-part of my copending Ser. No. 418,343, filed Dec. 14,1964, now US. Pat. No. 3,628,942.

This invention relates to stable, relatively concentrated herbicidalliquids which contain as their active ingredient herbicidally active3,5,6-substituted uracils. Specifically, the invention is directed tocompositions of the above type which contain phytotoxic aromatichydrocarbon oils and other known herbicides thereby providingherbicidally active unitary compositions capable of controllingvegetation when applied to the situs upon which said vegetation grows.This treatment allows such vegetation to be controlled at low economicdoses and in relatively short periods of time after application of thecompositions.

It has been recently discovered that certain 3,5,6- substituted uracilspossess a high degree of herbicidal activity. These chemicals arecrystalline solids which have only a slight solubility in liquidscommonly used as carriers for applying herbicidally active chemicals.For instance, carriers as water and inexpensive organic materials suchas aliphatic petroleum solvents will dis solve only minute amounts ofthe herbicidally active uracils. To the present, it has been necessaryto apply the herbicidally active 3,5,6-substituted uracils in the formof dust or granules or as so-called wettable powder formulations. Suchproducts are troublesome to prepare and difficult to apply at uniformrates. They are far inferior to true liquid formulations from a standpoint of applying these products to large areas such as are encounteredin the treatment of railroad right-of-i ways.

Another disadvantage that has been encountered iri the use ofherbicidally active 3,5,6-substituted uracils is that these products arerelatively slow in their initial destructive effect to undesirablevegetation. In manyl areas of weed control it is not only beneficial butneces-} sary that good control be achieved within a very short period oftime after application. Thus, if it were possible to provide aformulation containing herbicidally active 3,5,6-substituted uracilswhich was a readily ap-? plied liquid and which would have immediateeffect in the control of weeds, it would be a valuable contribu-} tionto the weed control art.

Another disadvantage sometimes encountered when using the herbicidallyactive 3,5,6-substituted uracils is that certain select species are noteradicated or controlled by these materials. When such situations occur,it would be helpful if it were possible to combine with the herbicidallyactive 3,5,6-substituted uracils other known herbicidally activechemicals which would tend to control these species. It, therefore, isan object of the invention to provide liquid herbicide formulationswhich contain herbicidally active 3,5,6-substituted uracils to allowrelatively complete control of a wide number of undesirable plantspecies.

A further object of the invention is to provide herbicidal compositionscontaining herbicidally active 3,5,6-substituted uracils either alone orin combination with other herbicidally active chemicals to provide quickacting herbicidally active products.

A still further object is to provide multicomponent hydrocarbon liquidcompositions containing substituted uracils, the contents of which maybe tailored according to the type of plant desired to be controlled.

It is intended that such materials be suitable for spraying operationsin whatever amounts are required for the desired extent of plant growthcontrol, such as in controlling weed problems found on or nearroadsides, railroad rights-of-way, industrial sites, and areas adjacentto cultivated land. Other objects will appear hereinafter.

In accordance with the invention, a quick acting liquid herbicidalcomposition comprising a herbicidally active 3,5,6-substituted uracilhas been discovered. The heretofore hydrocarbon-insoluble uracil isdissolved in a hydrocarbon oil, having an aromatic content calculated asat least percent, by cooperative action of a fatty acid co-solvent. Thefatty acid co-solvent acts as a coupling agent to unite the herbicidallyactive 3,5,6-substituted uracil with the phytotoxic hydrocarbon oil. Ina specific embodiment of the invention the uracil herbicide is combinedin liquid form with one or more additional herbicides other than theherbicidally active uracil material.

The compositions of the invention may be prepared in a variety of ways.For example, the uracil and fatty acid may be added to a heated aromatichydrocarbon oil and both materials simultaneously dissolved. In anotherembodiment, the uracil and fatty acid co-solvent may be admixed and theresultant premix added to a heated or unheated oil. For best results,the dissolution of uracil via fatty acid co-solvency effect is bestcarried out at a temperature of at least 40C. up to the boiling point ofany of the several components.

It is not exactly understood in what manner the fatty acid co-solventeffects dissolution of uracil in aromatic hydrocarbon oil. However, itis believed that the fatty acid acts as a bridging agent" due to itsbalanced hydrophilic-lipophilic ratio to thereby effectuate solution ofuracil in aromatic hydrocarbon oil.

Until the present invention, it was impossible to solubilizesubstituted-uracils in any substantial proportion in hydrocarbon media.Without benefit of a fatty acid co-solvent hydrocarbon solutionscontaining at least 5 percent uracil herbicide were impossible toachieve. in addition, even with benefit of fatty acid co-solvent3,5,6-substituted uracils are only difficultly soluble, if at all, inother hydrocarbon oils containing lower amounts of aromatic content. Inother cases the uracil, while initially soluble, does not remain so forappreciable durations of time. It is essential, therefore, in thepractice of the instant invention that the hydrocarbon solubilizingagent have an aromatic content of at least 60 percent to obtain auniform, long-lasting homogeneous solution of uracil via fatty acidco-solvent.

A preferred composition of the invention, Composition A below includesthe preferred range of parts by weight of the various ingredients whichgo to make up the novel uracil compositions of the invention.

The most preferred range of ingredients of the herbicidal compositionsis shown by the general formula set forth below as Composition B.

In following the above steps to produce herbicidally active liquidcompositions it is a further practice of the invention, in certaininstances, to add to those products other herbicides such as esters of2,4,5- trichlorophenoxyacetic acid, esters of 2,4- dichlorophenoxyaceticacid, pentachlorophenol, 2,3,6- trichlorobenzoic acid,2,methyl-4-chlorophenoxyacetic acid and methoxy 2,3,6-trichlorobenzoicacid.

For example, it is often desirable to combine Compositions A or B abovewith various other herbicides in order to both fortify the substituteduracils and/or overcome some of their inherent deficiencies in treatingvarious grasses or broad leaf plants. A few of the suitable combinationsof A and B with other herbicides are listed below. Many of theseherbicides are nonselective contact killers or sterilants. That is, theydestroy or retard the growth of both momocotyledonous and dicotyledonousplant species. Other materials listed are useful in inhibiting thegrowth of or destroying brush or grasses specifically. in someinstances, these herbicides show synergistic activity in promoting theactivity of the uracil in addition to exhibiting their own special typeof herbicidal activity.

Table 1 below shows the preferred herbicides which are used to fortifythe substituted uracils and their preferred weight composition whencombined with Compositions A or B to form a unitary herbicidal system.

TABLE I Generally, when one or more herbicides are used in addition tothe dissolved uracil the following ranges of ingredients are preferred.

Material by Weight Aromatic Oil 30-89 Uracil 5-20 Fatty Acid l-20Additional l-lerbicide(s) 5-30 With specific reference to the aboveherbicides, many esters of both trichlorophenoxyacetic anddichlorophenoxy acetic acids show herbicidal activity and particularutility in combination with the compositions of the invention. Among theesters of both of these acids are the iso-octyl esters, the propyleneglycol-bis esters, propylene glycol butyl ether esters, etc. Lastly,methoxy triazines are useful in the invention, and include 2-methoxy,4-isopropylamino, 6- isopropylamino triazine; 2-methoxy, 4-methylamino,6- isopropylamino triazine; 2-methoxy, 4-diethylamino, 6- isopropylaminotriazine; and Z-methoxy, 4-ethylamino, 6-ethylamino triazine. Mercaptotriazines such as 2- methyl mercapto, 4-ethylamino, 6-ethylaminotriazine, etc., are also useful.

The herbicidally active 3,5,6-substituted uracils which form anessential ingredient of the compositions of the invention fall withinthe following general structural formula:

herein X is a monovalent organic radical selected fiom the groupconsisting of hydrogen, alkyl, aralkyl, a karyl, hydroxyalkyl,thioalkyl, carboxyalkyl, and kyl ester radicals with the proviso thatthe radical contain not more than nine carbon atoms. Y and Z are rdicals chosen from the group consisting of halogen, itro, cyano, amino,alkoxyamino, alkyl, alkaryl, aralyl, phenylamino, aminophenyl andsulfonamide.

The various substituents on the basic uracil ring may e varied over awide range. That is to say, the radicals a tached to the heterocyclicring generally represented by X, Y, and Z may contain a wide spectrum offunct onal organic groups. Among these, a few are listed in able IIbelow.

X l. H, CH C 11 CH(CH 2. amount, CH2R 3. CH OH, CH CH OH 4. CH SH, CH CHSl-l 5. CH,COOH

6. CH COOC,H,,

l.Cl, Br,l

3. NH,, NH(OCH) 4. CH C H, CH

l Cl, Br, I 2. CH C l-l Cyclohexyl 3. NH- NH(OCH) HaCNH, 0 5015:

Other herbicidally active 3,5,6-substituted uracils are shown in BelgianPat. No. 625,897 the disclosure of which is incorporated herein byreference.

Specific uracil compounds which have found particular use in thepractices of the invention are listed below in Table III wherein theparticular substituents as expressed by X, Y, Z, comprising theparticular compounds are listed.

TABLE III Composition No. X Y

, Z l l 1 (CHQ CH Br QH,

2 CH Cl 1C! As has been discussed above, the herbicidally active uracilsof the above type listed materials are solubilized in a phytotoxichydrocarbon oil through the use of fatty acids which will be discussedin more detail below. The oil itself in the composition helps to giveextremely fast herbicidal control by searing or burning the undesirablevegetation upon immediate contact. In particular, it has been found thatthose hydrocarbon oils that should be used to both provide highlyconcentrated stable uracil solutions and finished herbicidalcompositions which are effective in controlling a wide spectrum ofannual or perennial broad leaf plants and/or grasses, are thosehydrocarbon oils which may be generically classified as aromaticpetroleum hydrocarbon solvents." Specifically, this type solventincludes those particular petroleum type solvents 'which contain atleast 60 percent by weight of aromatic components and more preferably,65 percent by weight or more. Most preferably, the hydrocarbon oilsolvent should have an aromatic content of 70-95 percent.

. End Point Exemplary solvents of this type are listed in Table IV asfollows: For convenience, the specifications of these typical industrialaromatic type oils are included. These oils are all extremely economicalto use and would add little or no cost to the composition employingsame.

TABLE IV Specifications Specific Gravity at 60F. Flash Point PMCCAromatic Content Color ASTM A B C E Pale Amber 5.0 Green Aniline PointMixed 88F 78F Mixed 66F Sulfur Viscosity S.U. at lOOF. ASTM DistillationI.B.P. F. 10% Reco vcrcd 50% Recovcrcd 90% Recovcrcd 488 748Pentachlorophenol Solution at 40F. l5.0 12.5 15.0

Desired Specifications Specific Gravity at 60F. Flash Point PMCCAromatics l.00 or slightly lower 225F. or lowcr Maximum amount at leastMinimum amount Sweet 0F. or lower (No sludging or pronounced thickeningdown to 32 F.)

Viscosity S.U.S. at F. Odor Pour Point With respect to the fatty acidco-solvent preferred materials contain at least 4 carbon atoms. The mostpreferred co-solvents are the well-known unsaturated aliphatic fattyacids which contain at least 12 carbon atoms in an aliphatic chain.Exemplary of such materials are listed below:

Linolcic Lauroleic Myristoleic Linolenic Palmitolcic Elcosteric OleicLicanic Gadoleic Arachidnnic Erucic Clupanodonic Ricinoleic animal orvegetable sources, for example, lard, coconut oil, tall oil, rapeseedoil, sesame oil, palm kernel oil, palm oil, olive oil, corn oil,cottonseed oil, sardine oil, tallow, soybean oil, peanut oil, castoroil, seal oil, whale oil, shark oil and other fish oils, teaseed oil,partially or completely hydrogenated animal and vegetable oils, such asthose mentioned; hydroxy and alpha-hydroxy fatty acids, such ashydroxystearic acid, dihydroxypalmitic acid, dihydroxystearic acid,dihydroxybehenic acid, alphahydroxy capric acid, alphahydroxy stearicacid, alphahydroxy palmitic acid, alphahydroxy lauric acid, alphahydroxymyristic acid, alphahydroxy coconut oil mixed fatty acids,alphahydroxy-margaric acid, alphahydroxy arachidic acid, and the like;fatty acids derived from various waxes, such as beeswax, spermaceti,montan wax, Japan wax, cocerin, and carnauba wax. Such acids includecarnaubic acid, cerotic acid, lacceric acid, montanic acid,psyllastearic acid, etc.

Utilizing the chemicals described above there is listed below a typicalcomposition of the invention:

COMPOSITION C Constituent by Weight 3-sec brityl-S-bromo, 6-methyluracil l0.0 Tall oil fatty acid 10.0 Oil C of Table III 80.0

To the basic compositions of the invention may be added various otheringredients. A typical composition containing added active ingredientsused to fortify the oil solubilized substituted uracil compounds is asfollows:

COMPOSITION D Constituent by Weight 3-sec butyl, S-bromo, 6-methyluracil 10.0 Tall oil fatty acid 10.0 Oil C of Table III 61.5

lsoctyl ester of 2,4-dichlorophcnoxyacetic acid Pentachlorophenol In acomparative test, fresh uracil in form of dust was also employed inequal active concentrations expressed in pounds per acre. It was notedthat the hydrocarbon oil solution exhibited as much long duration killactivity as did the unformulated uracil sample. This is proof of thecontention that uracil herbicidal activity is not lost through solutionin aromatic hydrocarbon oil via cosolvency effect of the fatty acid. Inaddition, the hydrocarbon oil composition of the invention containinguracil gave immediate contact kill due to presence of phytotoxichydrocarbon oil. The uracil applied in dust form gave substantially noimmediate kill results.

In another series of comparative runs, the concentrates of the inventionwere further diluted with additional oil, and applied to broad leaf andgrass sites in active uracil concentrations ranging from about 0.5 toabout 1.0 percent by weight. Aqueous suspensions of the same uracil, andin the same dosages, exhibited poor results with respect to visual killof broad leaf and grass test samples. In some instances, via visualreadings of the hydrocarbon-based uracil sample results vs. results withaqueous suspensions of uracil d monstrated that the former solutionswere manyfold ti es greater in effectiveness. Thus, two important advntages of the invention have been realized by applic tion of a unitaryuracil hydrocarbon composition; n mely, both immediate contact kill aswell as long te duration residual kill and growth inhibition are exhi bi fed. Such aims can best be accomplished by synthesi and use of ahomogeneous solution of uracil in a pfiytotoxic hydrocarbon oil havingan aromatic h drocarbon of at least percent.

In another test series, sole application of a hydrocarb n oil wascompletelyineffectual with regard to preemergence effect; that is,application of hydrocarb n oil of the type listed above had no effectwhatso ver upon seed germination. On the other hand, the cotnpositionsof the invention comprising both uracil an phytotoxic hydrocarbon oilhad an excellent pr emergence effect upon a variety of plants to the pont where almost complete kill was shown even at the en of the testingperiod. As well, such compositions exhibited excellent initialpost-emergence effectiveness or weed control activity upon visiblegrowth. Thus, only through solubilization of uracil via the novelsolvent system discussed above can a substituted uracil be uniformlyapplied such as by spraying in presence of a hydrocarbon oil to give anacceptable contact kill in addition to a long term lasting effect. Afterthe initial destruction or inhibition of growth has taken place throughthe medium of the phytotoxic oil, a continued killing effect isprimarily derived from the reactivity of the uracil and other herbicidalingredients of the compositions of the invention. The contact killeffect of the oil in essence enhances the overall action of the activeherbicide ingredients in destroying, retarding or preventing regrowthsof vegetation.

order to enhance the wetting effect and produce better dispersion of theactive herbicidal material on the vegetation to which it is applied. Itwill be understood, however, that such auxiliary agents are notnecessary and can be omitted in the practical application of theinvention.

It is obvious that various ramifications and modifications of theinstant invention can be made in the light of the instant disclosure.

What is claimed is:

l. A quick acting liquid herbicidal composition comprising a majoramount of a hydrocarbon oil having an aromatic content of at least 60percent, and a herbicidally-active 3,5,6-substituted uracil dissolvedtherein by means of a fatty acid co-solvent, wherein said fatty acidco-solvent is at least 12 carbon atoms in chain length.

2. A quick acting liquid herbicidal composition comprising 60 to 94percent by weight of a hydrocarbon oil having an aromatic content of atleast 60 percent, and 5 to 20 percent by weight of a herbicidally active3,5,6- substituted uracil dissolved therein by means of l to 20 percentby weight of a fatty acid co-solvent, wherein said fatty acid co-solventis at least 12 carbon atoms in chain length. I

3. A quick acting liquid herbicidal composition comprising 30 to 89percent of a hydrocarbon oil having an aromatic content of at least 60percent, 5 to 20 percent of a herbicidally active 3,5,6-substituteduracil dissolved therein by means of 1 to 20 percent by weight of afatty acid co-solvent wherein said fatty acid co-solvent is at least 12carbon atoms in chain length and 5 to 30 percent by weight of at leastone additional herbicide other than said uracil.

2. A quick acting liquid herbicidal composition comprising 60 to 94percent by weight of a hydrocarbon oil having an aromatic content of atleast 60 percent, and 5 to 20 percent by weight of a herbicidally active3,5,6-substituted uracil dissolved therein by means of 1 to 20 percentby weight of a fatty acid co-solvent, wherein said fatty acid co-solventis at least 12 carbon atoms in chain length.
 3. A quick acting liquidherbicidal composition comprising 30 to 89 percent of a hydrocarbon oilhaving an aromatic content of at least 60 percent, 5 to 20 percent of aherbicidally active 3,5,6-substituted uracil dissolved therein by meansof 1 to 20 percent by weight of a fatty acid co-solvent wherein saidfatty acid co-solvent is at least 12 carbon atoms in chain length and 5to 30 percent by weight of at least one additional herbicide other thansaid uracil.